Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Benzene, 1-bromo-4-(trifluoromethyl)- | HCID 67872 | — |
| Reactant | tert-Butyl piperazine-1-carboxylate | HCID 143452 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Catalyst | Tri-o-tolylphosphine | HCID 80271 | — |
| Catalyst | (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | HCID 6505921 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 23081333 | HCID 23081333 | 87% |
Reaction Steps
A mixture of 4-bromobenzotrifluoride (3.0 g, 13.3 mmol), tert-butyl piperazine-1-carboxylate (2.9 g, 15.3 mmol), bis(dibenzylideneacetone)palladium (306 mg, 0.53 mmol), tri-o-tolylphosphine (162 mg, 0.53 mmol), and sodium tert-butoxide (2.2 g, 22.7 mmol) in toluene (60 ml) was refluxed under a nitrogen atmosphere for 4 hours. Ethyl acetate and water were added to the reaction mixture, which was stirred for a while, and the insoluble substances were removed by filtration through Celite, and the filtrate was then extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/methylene chloride=2/1) to afford tert-butyl 4-(4-trifluoromethylphenyl)-piperazine-1-carboxylate (3.8 g, yield 87%) as a white powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07262212B2 |
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| Source dataset | uspto-grants-2007_08 |
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| ORD ID | ord-a993bccab943457f9845bd8d65c64de7 |
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| Source note | uspto-grants-2007_08 |
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